Nguyen Vu T, Haug Graham C, Nguyen Viet D, Vuong Ngan T H, Arman Hadi D, Larionov Oleg V
Department of Chemistry, The University of Texas at San Antonio One UTSA Circle San Antonio TX 78249 USA
Chem Sci. 2021 Apr 13;12(18):6429-6436. doi: 10.1039/d1sc01389k.
Sulfonamides feature prominently in organic synthesis, materials science and medicinal chemistry, where they play important roles as bioisosteric replacements of carboxylic acids and other carbonyls. Yet, a general synthetic platform for the direct conversion of carboxylic acids to a range of functionalized sulfonamides has remained elusive. Herein, we present a visible light-induced, dual catalytic platform that for the first time allows for a one-step access to sulfonamides and sulfonyl azides directly from carboxylic acids. The broad scope of the direct decarboxylative amidosulfonation (DDAS) platform is enabled by the efficient direct conversion of carboxylic acids to sulfinic acids that is catalyzed by acridine photocatalysts and interfaced with copper-catalyzed sulfur-nitrogen bond-forming cross-couplings with both electrophilic and nucleophilic reagents.
磺胺类化合物在有机合成、材料科学和药物化学中占据显著地位,在这些领域中,它们作为羧酸和其他羰基的生物电子等排体替代物发挥着重要作用。然而,将羧酸直接转化为一系列功能化磺胺类化合物的通用合成平台仍然难以实现。在此,我们展示了一个可见光诱导的双催化平台,该平台首次实现了直接从羧酸一步制备磺胺类化合物和磺酰叠氮化物。直接脱羧酰胺磺化(DDAS)平台的广泛适用性是通过吖啶光催化剂催化羧酸高效直接转化为亚磺酸,并与铜催化的与亲电试剂和亲核试剂形成硫氮键的交叉偶联反应相结合而实现的。